organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Ethyl 4,9-di­methyl-9H-carbazole-3-carboxyl­ate

aDokuz Eylül University, Faculty of Arts and Sciences, Department of Chemistry, Tınaztepe, 35160 Buca, İzmir, Turkey, bAksaray University, Department of Physics, 68100, Aksaray, Turkey, cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and dHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 23 January 2014; accepted 29 January 2014; online 5 February 2014)

In the title compound, C17H17NO2, the carbazole skeleton includes an eth­oxy­carbonyl group at the 3-position. The indole three-ring system is almost planar [maximum deviation = 0.065 (2) Å], and the ethyl ester group is inclined to its mean plane by 15.48 (2)°. In the crystal, there are ππ stacking inter­actions between parallel benzene rings and between parallel benzene and pyrrole rings of adjacent mol­ecules [centroid–centroid distances = 3.9473 (8) and 3.7758 (8) Å, respectively]. Weak C—H⋯π inter­actions are also present.

Related literature

For the first isolation of carbazole from coal tar, see: Graebe & Glazer (1872[Graebe, C. & Glazer, C. (1872). Ber. Dtsch Chem. Ges. 5, 12.]). For the isolation of murrayanine, the first report of a naturally occurring carbazole alkaloid, see: Chakraborty et al. (1965[Chakraborty, D. P., Barman, B. K. & Bose, P. K. (1965). Tetrahedron, 21, 681-685.]). For the intriguing structural features and promising biological activities exhibited by many carbazole alkaloids, see: Chakraborty (1993[Chakraborty, D. P. (1993). The Alkaloids: Chemistry and Pharmacology. edited by G. A. Cordell, Vol. 44, pp. 257-364. New York: Academic Press.]). For the syntheses of pyridocarbazoles, see: Karmakar et al. (1991[Karmakar, A. C., Gandhi, K. K. & Jayanta, K. R. (1991). J. Chem. Soc. Perkin Trans. 1, pp. 1997-2002.]). For related structures, see: Hökelek et al. (1994[Hökelek, T., Patır, S., Gülce, A. & Okay, G. (1994). Acta Cryst. C50, 450-453.]); Patır et al. (1997[Patır, S., Okay, G., Gülce, A., Salih, B. & Hökelek, T. (1997). J. Heterocycl. Chem. 34, 1239-1242.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C17H17NO2

  • Mr = 267.32

  • Orthorhombic, P b c a

  • a = 14.5228 (5) Å

  • b = 12.4663 (4) Å

  • c = 15.2354 (5) Å

  • V = 2758.30 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.43 × 0.35 × 0.25 mm

Data collection
  • Bruker SMART BREEZE CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.979

  • 61052 measured reflections

  • 2798 independent reflections

  • 2358 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.133

  • S = 1.07

  • 2798 reflections

  • 185 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of rings N9/C8A/C5A/C4A/C9A, C1–C4/C4A/C9A, and C5/C5A/C8A/C8/C7/C6, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯Cg1i 0.93 2.83 3.7091 (17) 159
C13—H13ACg2ii 0.97 2.91 3.6381 (17) 133
C14—H14CCg3ii 0.96 2.73 3.580 (2) 149
Symmetry codes: (i) [x, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Carbazole was firstly isolated from coal tar many years ago (Graebe & Glazer, 1872). The isolation of murrayanine was the first report of a naturally occurring carbazole alkaloid (Chakraborty et al., 1965). Since then there has been a strong interest in this area by chemists and biologists due to the intriguing structural features and promising biological activities exhibited by many carbazole alkaloids (Chakraborty, 1993). Most carbazole alkaloids have been isolated from the taxonomically related higher plants of the genus Murraya, Glycosmis and Clausena from the family Rutaceae. The genus Murraya represents the richest source of carbazole alkaloids from terrestrial plants. The title compound was used as a precursor compound for the syntheses of pyridocarbazoles (Karmakar et al., 1991) and we report herein on its crystal structure.

The molecule of the title compound, Fig. 1, contains a carbazole skeleton with an ethoxycarbonyl group at the 3 position. The bond lengths are close to standard values (Allen et al., 1987) and generally agree with those in previously reported compounds (Hökelek et al., 1994; Patır et al., 1997). In all structures atom N9 is substituted.

An examination of the deviations from the least-squares planes through individual rings shows that rings A (C1—C4/C4a/c9a), B (C4a/C5a/C8a/N9/C9a) and C (C5a/C5—C8/C8a) are nearly coplanar [with a maximum deviation of 0.065 (2) Å for atom C7] with dihedral angles of A/B = 2.41 (4) °, A/C = 4.01 (4) ° and B/C = 1.63 (5) °. Atoms C10, C11 and C12 are displaced by -0.059 (2), -0.092 (2) and 0.079 (2) Å from the adjacent ring planes.

In the crystal, ππ contacts between the benzene rings and between the benzene and pyrrole rings, Cg1···Cg1i and Cg2···Cg1i [symmetry code: (i) 1 - x, - y, 1 - z, where Cg1 and Cg2 are the centroids of the rings A (C1—C4/C4a/C9a) and B (C4a/C5a/C8a/N9/C9a), respectively] stabilize the crystal structure, with centroid-centroid distances of 3.9473 (8) and 3.7758 (8) Å. The weak C—H···π interactions (Table 1) may be further effective in the stabilization of the crystal structure.

Related literature top

For the first isolation of carbazole from coal tar, see: Graebe & Glazer (1872). For the isolation of murrayanine, the first report of a naturally occurring carbazole alkaloid, see: Chakraborty et al. (1965). For the intriguing structural features and promising biological activities exhibited by many carbazole alkaloids, see: Chakraborty (1993). For the syntheses of pyridocarbazoles, see: Karmakar et al. (1991). For related structures, see: Hökelek et al. (1994); Patır et al. (1997). For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of ethyl 4-methyl-9H-carbazole-3-carboxylate (2.50 g, 10 mmol), potassium hydroxide (1.70 g, 30 mmol) and methyl iodide (1.25 ml, 20 mmol) in acetone (100 ml) was stirred at 273 K for 2 h, and then acidified with HCl (6N). The aqueous layer was extracted with dichloromethane. The combined organic phases were dried with magnesium sulfate, filtered, and the solvents were evaporated. The residue was purified by column chromatography using silica gel, hexane/ethyl acetate (1:1). After the solvent was evaporated, the crude product was recrystallized from methanol (yield 87%, M.p. 383 K), giving colourless prismatic crystals.

Refinement top

The C-bound H-atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å, for aromatic, methylene and methyl H-atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = k × Ueq(C), where k = 1.5 for methyl H-atoms and = 1.2 for other H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the crystal packing of the title compound [H-atoms have been omitted for clarity].
Ethyl 4,9-dimethyl-9H-carbazole-3-carboxylate top
Crystal data top
C17H17NO2F(000) = 1136
Mr = 267.32Dx = 1.287 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9733 reflections
a = 14.5228 (5) Åθ = 2.5–28.6°
b = 12.4663 (4) ŵ = 0.08 mm1
c = 15.2354 (5) ÅT = 296 K
V = 2758.30 (16) Å3Prism, colourless
Z = 80.43 × 0.35 × 0.25 mm
Data collection top
Bruker SMART BREEZE CCD
diffractometer
2798 independent reflections
Radiation source: fine-focus sealed tube2358 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 1818
Tmin = 0.965, Tmax = 0.979k = 1515
61052 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0716P)2 + 0.6943P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2798 reflectionsΔρmax = 0.23 e Å3
185 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0071 (10)
Crystal data top
C17H17NO2V = 2758.30 (16) Å3
Mr = 267.32Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.5228 (5) ŵ = 0.08 mm1
b = 12.4663 (4) ÅT = 296 K
c = 15.2354 (5) Å0.43 × 0.35 × 0.25 mm
Data collection top
Bruker SMART BREEZE CCD
diffractometer
2798 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
2358 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.979Rint = 0.041
61052 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.07Δρmax = 0.23 e Å3
2798 reflectionsΔρmin = 0.18 e Å3
185 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.41026 (9)0.81153 (11)0.06716 (8)0.0672 (4)
O20.46532 (8)0.86264 (9)0.06240 (7)0.0529 (3)
C10.62278 (10)0.60151 (12)0.10399 (9)0.0442 (4)
H10.64690.59020.15980.053*
C20.56446 (10)0.68566 (12)0.08727 (9)0.0430 (3)
H20.54840.73120.13310.052*
C30.52798 (9)0.70562 (11)0.00294 (9)0.0396 (3)
C40.55188 (9)0.63966 (12)0.06812 (9)0.0392 (3)
C4A0.60974 (9)0.55202 (11)0.05131 (8)0.0376 (3)
C50.63676 (11)0.43336 (14)0.19289 (10)0.0503 (4)
H50.60280.47490.23200.060*
C5A0.64528 (9)0.46499 (12)0.10518 (9)0.0404 (3)
C60.67876 (12)0.34056 (15)0.22115 (11)0.0585 (4)
H60.67300.32000.27960.070*
C70.72949 (12)0.27711 (15)0.16397 (12)0.0585 (4)
H70.75680.21460.18470.070*
C80.74011 (11)0.30520 (13)0.07687 (11)0.0507 (4)
H80.77440.26300.03860.061*
C8A0.69762 (9)0.39910 (12)0.04852 (10)0.0419 (3)
N90.69734 (8)0.44270 (10)0.03478 (8)0.0430 (3)
C9A0.64444 (9)0.53372 (11)0.03426 (9)0.0392 (3)
C100.74717 (13)0.40054 (15)0.10959 (11)0.0575 (4)
H10A0.73970.32410.11200.086*
H10B0.81140.41760.10390.086*
H10C0.72350.43200.16250.086*
C110.52039 (12)0.66026 (15)0.16070 (10)0.0564 (4)
H11A0.56900.64240.20080.085*
H11B0.46740.61680.17320.085*
H11C0.50470.73460.16720.085*
C120.46242 (10)0.79659 (12)0.00684 (9)0.0441 (3)
C130.39819 (11)0.94836 (13)0.06466 (11)0.0515 (4)
H13A0.33660.92000.05670.062*
H13B0.41040.99990.01840.062*
C140.40701 (16)0.99994 (19)0.15226 (13)0.0778 (6)
H14A0.39470.94800.19730.117*
H14B0.46841.02730.15920.117*
H14C0.36371.05780.15680.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0694 (8)0.0763 (9)0.0559 (7)0.0237 (7)0.0186 (6)0.0033 (6)
O20.0516 (6)0.0491 (7)0.0579 (7)0.0120 (5)0.0104 (5)0.0057 (5)
C10.0473 (8)0.0509 (9)0.0345 (7)0.0007 (7)0.0044 (5)0.0033 (6)
C20.0446 (7)0.0460 (8)0.0383 (7)0.0001 (6)0.0004 (6)0.0006 (6)
C30.0356 (7)0.0423 (8)0.0408 (7)0.0030 (6)0.0010 (5)0.0033 (6)
C40.0352 (6)0.0435 (8)0.0390 (7)0.0055 (6)0.0030 (5)0.0036 (6)
C4A0.0334 (6)0.0419 (8)0.0374 (7)0.0071 (6)0.0005 (5)0.0025 (5)
C50.0458 (8)0.0594 (10)0.0458 (8)0.0044 (7)0.0038 (6)0.0060 (7)
C5A0.0338 (6)0.0436 (8)0.0437 (7)0.0063 (6)0.0006 (5)0.0001 (6)
C60.0559 (9)0.0665 (11)0.0532 (9)0.0073 (8)0.0007 (7)0.0171 (8)
C70.0534 (9)0.0508 (10)0.0712 (11)0.0027 (8)0.0062 (8)0.0153 (8)
C80.0441 (8)0.0451 (9)0.0628 (9)0.0004 (6)0.0019 (7)0.0011 (7)
C8A0.0355 (7)0.0426 (8)0.0476 (7)0.0064 (6)0.0019 (5)0.0014 (6)
N90.0436 (7)0.0442 (7)0.0413 (6)0.0027 (5)0.0027 (5)0.0040 (5)
C9A0.0358 (7)0.0416 (8)0.0401 (7)0.0031 (6)0.0009 (5)0.0049 (6)
C100.0607 (10)0.0618 (11)0.0501 (9)0.0137 (8)0.0077 (7)0.0093 (8)
C110.0616 (10)0.0654 (11)0.0422 (8)0.0109 (8)0.0111 (7)0.0006 (7)
C120.0407 (7)0.0477 (8)0.0441 (7)0.0008 (6)0.0009 (6)0.0034 (6)
C130.0504 (9)0.0475 (9)0.0567 (9)0.0118 (7)0.0059 (7)0.0034 (7)
C140.0905 (15)0.0754 (14)0.0675 (12)0.0381 (12)0.0201 (10)0.0156 (10)
Geometric parameters (Å, º) top
O1—C121.2054 (18)C8—C71.381 (2)
O2—C121.3388 (18)C8—H80.9300
O2—C131.4469 (18)C8A—C81.392 (2)
C1—H10.9300N9—C8A1.3805 (19)
C2—C11.372 (2)N9—C9A1.3704 (18)
C2—H20.9300N9—C101.4488 (19)
C3—C21.4119 (19)C9A—C11.393 (2)
C3—C121.488 (2)C10—H10A0.9600
C4—C31.403 (2)C10—H10B0.9600
C4—C111.5049 (19)C10—H10C0.9600
C4A—C41.402 (2)C11—H11A0.9600
C4A—C5A1.455 (2)C11—H11B0.9600
C4A—C9A1.4162 (18)C11—H11C0.9600
C5—C61.377 (2)C13—C141.487 (2)
C5—H50.9300C13—H13A0.9700
C5A—C51.399 (2)C13—H13B0.9700
C5A—C8A1.413 (2)C14—H14A0.9600
C6—C71.388 (3)C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
C7—H70.9300
C12—O2—C13116.86 (12)C8A—N9—C10125.37 (13)
C2—C1—C9A117.48 (13)C9A—N9—C8A108.81 (11)
C2—C1—H1121.3C9A—N9—C10125.80 (13)
C9A—C1—H1121.3N9—C9A—C1128.64 (12)
C1—C2—C3122.36 (13)N9—C9A—C4A109.76 (12)
C1—C2—H2118.8C1—C9A—C4A121.59 (13)
C3—C2—H2118.8N9—C10—H10A109.5
C2—C3—C12117.74 (13)N9—C10—H10B109.5
C4—C3—C2120.40 (13)N9—C10—H10C109.5
C4—C3—C12121.85 (12)H10A—C10—H10B109.5
C3—C4—C11123.23 (13)H10C—C10—H10A109.5
C4A—C4—C3117.65 (12)H10C—C10—H10B109.5
C4A—C4—C11119.11 (13)C4—C11—H11A109.5
C4—C4A—C5A133.68 (12)C4—C11—H11B109.5
C4—C4A—C9A120.47 (13)C4—C11—H11C109.5
C9A—C4A—C5A105.84 (12)H11B—C11—H11A109.5
C5A—C5—H5120.1H11B—C11—H11C109.5
C6—C5—C5A119.77 (15)H11C—C11—H11A109.5
C6—C5—H5120.1O1—C12—O2121.70 (14)
C5—C5A—C4A135.87 (14)O1—C12—C3126.58 (14)
C5—C5A—C8A117.86 (14)O2—C12—C3111.69 (12)
C8A—C5A—C4A106.23 (12)O2—C13—C14106.43 (13)
C5—C6—C7121.17 (15)O2—C13—H13A110.4
C5—C6—H6119.4O2—C13—H13B110.4
C7—C6—H6119.4C14—C13—H13A110.4
C8—C7—C6121.18 (16)C14—C13—H13B110.4
C8—C7—H7119.4H13B—C13—H13A108.6
C6—C7—H7119.4C13—C14—H14A109.5
C7—C8—C8A117.51 (16)C13—C14—H14B109.5
C7—C8—H8121.2C13—C14—H14C109.5
C8A—C8—H8121.2H14B—C14—H14A109.5
N9—C8A—C5A109.34 (13)H14B—C14—H14C109.5
N9—C8A—C8128.14 (14)H14C—C14—H14A109.5
C8—C8A—C5A122.52 (14)
C13—O2—C12—O14.5 (2)C5A—C4A—C9A—N90.13 (15)
C13—O2—C12—C3174.05 (12)C5A—C4A—C9A—C1178.99 (13)
C12—O2—C13—C14172.34 (16)C5A—C5—C6—C70.2 (2)
C3—C2—C1—C9A1.0 (2)C4A—C5A—C5—C6177.19 (15)
C4—C3—C2—C11.0 (2)C8A—C5A—C5—C60.0 (2)
C12—C3—C2—C1177.59 (13)C4A—C5A—C8A—N91.47 (15)
C2—C3—C12—O1162.94 (16)C4A—C5A—C8A—C8177.90 (13)
C2—C3—C12—O215.50 (18)C5—C5A—C8A—N9179.47 (13)
C4—C3—C12—O115.7 (2)C5—C5A—C8A—C80.1 (2)
C4—C3—C12—O2165.90 (13)C5—C6—C7—C80.4 (3)
C4A—C4—C3—C22.4 (2)C8A—C8—C7—C60.4 (2)
C4A—C4—C3—C12176.15 (12)N9—C8A—C8—C7179.14 (15)
C11—C4—C3—C2176.05 (14)C5A—C8A—C8—C70.1 (2)
C11—C4—C3—C125.4 (2)C9A—N9—C8A—C5A1.42 (15)
C5A—C4A—C4—C3176.61 (14)C9A—N9—C8A—C8177.90 (14)
C5A—C4A—C4—C114.9 (2)C10—N9—C8A—C5A176.89 (14)
C9A—C4A—C4—C31.83 (19)C10—N9—C8A—C83.8 (2)
C9A—C4A—C4—C11176.69 (13)C8A—N9—C9A—C1177.97 (14)
C4—C4A—C5A—C50.2 (3)C8A—N9—C9A—C4A0.79 (15)
C4—C4A—C5A—C8A177.64 (14)C10—N9—C9A—C13.7 (2)
C9A—C4A—C5A—C5178.42 (16)C10—N9—C9A—C4A177.52 (14)
C9A—C4A—C5A—C8A0.96 (14)N9—C9A—C1—C2177.05 (14)
C4—C4A—C9A—N9178.70 (12)C4A—C9A—C1—C21.6 (2)
C4—C4A—C9A—C10.2 (2)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of rings N9/C8A/C5A/C4A/C9A, C1–C4/C4A/C9A, and C5/C5A/C8A/C8/C7/C6, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg1i0.932.833.7091 (17)159
C13—H13A···Cg2ii0.972.913.6381 (17)133
C14—H14C···Cg3ii0.962.733.580 (2)149
Symmetry codes: (i) x, y3/2, z1/2; (ii) x, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of rings N9/C8A/C5A/C4A/C9A, C1–C4/C4A/C9A, and C5/C5A/C8A/C8/C7/C6, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg1i0.932.833.7091 (17)159
C13—H13A···Cg2ii0.972.913.6381 (17)133
C14—H14C···Cg3ii0.962.733.580 (2)149
Symmetry codes: (i) x, y3/2, z1/2; (ii) x, y+1/2, z+3/2.
 

Acknowledgements

The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization).

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